LIPID MAPS

Structure Database (LMSD)

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Common Name

3-hydroxy caprylic acid

Systematic Name

3-hydroxy-octanoic acid

Synonyms

LM ID

LMFA01050021

Formula

C₈H₁₆O₃

Exact Mass

Calculate m/z

160.109945

Sum Composition

FA 8:0;O

Status

Curated

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Classification

Biological Context

3-hydroxy Octanoic acid is a hydroxylated fatty acid that has been found in LPS from P. aeruginosa and the methyl-branched poly(3-hydroxyalkanoate) (PHA) polymers produced by P. oleovorans.^1,2 It is an agonist of the orphan receptor GPR109B, increasing intracellular calcium in human neutrophils which endogenously express GPR109B.³ 3-hydroxy Octanoic acid prevents lipolysis of human adipocytes and is upregulated in human plasma in response to a ketogenic diet. Plasma levels of 3-hydroxy Octanoic acid also increase 3.41-fold in human male runners following a treadmill run to exhaustion as well as in a mouse model of autism spectrum disorder (ASD) fed a high-glycemic diet.^4,5 [Matreya, LLC. Catalog No. 1745]

This information has been provided by Cayman Chemical

References

1. Currais, A., Farrokhi, C., Dargusch, R., et al. Dietary glycemic index modulates the behavioral and biochemical abnormalities associated with autism spectrum disorder. Mol. Psychiatry 21(3), 426-436 (2016).

2. Nieman, D.C., Sha, W., and Pappan, K.L. IL-6 linkage to exercise-induced shifts in lipid-related metabolites: A metabolomics-based analysis. J. Proteme Res. 16(2), 970-977 (2017).

3. Ahmed, K., Tunaru, S., Langhans, C.-D., et al. Deorphanization of GPR109B as a receptor for the β-oxidation intermediate 3-OH-octanoic acid and its role in the regulation of lipolysis. J. Biol. Chem. 284(33), 21928-21933 (2009).

4. Hazer, B., Lenz, R.W., and Fuller, R.C. Biosynthesis of methyl-branched poly(β-hydroxyalkanoate)s by Pseudomonas oleovorans. Macromol. 27(1), 45-49 (1994).

5. Uhlig, S., Negård, M., Heldal, K.K., et al. Profiling of 3-hydroxy fatty acids as environmental markers of endotoxin using liquid chromatography coupled to tandem mass spectrometry. J. Chromatogr. A 1434, 119-236 (2016).